PE(14:1(9Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))

(2-aminoethoxy)[(2R)-3-[(9Z)-tetradec-9-enoyloxy]-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphinic acid

Formula: C39H66NO11P (755.4373)
Chinese Name:
BioDeep ID: BioDeep_00000185740 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCC\C=C/CCCC)(COP(O)(=O)OCCN)OC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC



Found 16 Sample Hits

m/z Adducts Species Organ Scanning Sample
738.4336 [M+H-H2O]+
PPM:0.6
Mus musculus Lung MALDI (DHB)
image1 - MTBLS2075
Resolution: 40μm, 187x165

Description

Fig. 2 MALDI-MSI data from the same mouse lung tissue analyzed in Fig. 1. A: Optical image of the post-MSI, H&E-stained tissue section. B–D, F–G: Ion images of (B) m/z 796.6855 ([U13C-DPPC+Na]+), (C) m/z 756.5514 ([PC32:0+Na]+), (D) m/z 765.6079 ([D9-PC32:0+Na]+), (F) m/z 754.5359 ([PC32:1+Na]+), and (G) m/z 763.5923 ([D9-PC32:1+Na]+). E, H: Ratio images of (E) [D9-PC32:0+Na]+:[PC32:0+Na]+ and (H) [D9-PC32:1+Na]+:[PC32:1+Na]+. Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. U13C-DPPC, universally 13C-labeled dipalmitoyl PC; PC, phosphatidylcholine; MSI, mass spectrometry imaging; H&E, hematoxylin and eosin. Fig 1-3, Fig S1-S3, S5

720.4141 [M+H-2H2O]+
PPM:13
Mus musculus Left upper arm MALDI (CHCA)
357_l_total ion count - Limb defect imaging - Monash University
Resolution: 50μm, 97x131

Description

Diseased

738.4276 [M+H-H2O]+
PPM:8.7
Mus musculus Lung MALDI (DHB)
image5 - MTBLS2075
Resolution: 40μm, 163x183

Description

Supplementary Figure S8. MALDI-MSI data of mouse lung tissue administered with D9-choline and U 13C-DPPC–containing Poractant alfa surfactant (labels administered 18 h prior to sacrifice). Ion images of (a) m/z 796.6856 ([U13C-DPPC+Na]+), (b) m/z 756.5154 [PC32:0+Na]+ and (c) m/z 765.6079 ([D9-PC32:0+Na]+). (d) Overlay image of [U13C-DPPC+Na]+ (red) and [D9-PC32:0+Na]+ (green). Parts per million (ppm) mass errors are indicated in parentheses. All images were visualised using totalion-current normalisation and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0.

720.4098 [M+H-2H2O]+
PPM:19
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

778.4244 [M+Na]+
PPM:2.8
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

720.4115 [M+H-2H2O]+
PPM:16.6
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

778.4253 [M+Na]+
PPM:1.6
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

778.4245 [M+Na]+
PPM:2.6
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

720.4097 [M+H-2H2O]+
PPM:19.1
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

778.4244 [M+Na]+
PPM:2.8
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

720.41 [M+H-2H2O]+
PPM:18.7
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

778.4271 [M+Na]+
PPM:0.7
Mus musculus brain MALDI (DHB)
Brain01_Bregma-3-88b_centroid - MTBLS313
Resolution: 17μm, 265x320

Description

778.4289 [M+Na]+
PPM:3
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_02_centroid - MTBLS313
Resolution: 17μm, 434x258

Description

778.4284 [M+Na]+
PPM:2.4
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_01_centroid - MTBLS313
Resolution: 17μm, 447x118

Description

778.4269 [M+Na]+
PPM:0.5
Mus musculus brain MALDI (DHB)
Brain02_Bregma1-42_03 - MTBLS313
Resolution: 17μm, 483x403

Description

778.4268 [M+Na]+
PPM:0.3
Mus musculus brain MALDI (DHB)
Brain02_Bregma-1-46 - MTBLS313
Resolution: 17μm, 294x399

Description


PE(14:1(9Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) is an oxidized phosphatidylethanolamine (PE). Oxidized phosphatidylethanolamines are glycerophospholipids in which a phosphorylethanolamine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylethanolamines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidylethanolamines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PE(14:1(9Z)/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)), in particular, consists of one chain of one 9Z-tetradecenoyl at the C-1 position and one chain of Lipoxin A5 at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PEs can be synthesized via three different routes. In one route, the oxidized PE is synthetized de novo following the same mechanisms as for PEs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PE backbone, mainly through the action of LOX (PMID: 33329396).